Registration

New

Annoucement

Call for ContributionsHETEROCYCLES Special Issue Vol. 99 in honor of Professor Tohru Fukuyama on 70th Birthday

Submission deadline: September 10, 2018
On the occasion of Professor Tohru Fukuyama's 70th birthday, HETEROCYCLES editorial office is planning to publish special anniversary issue on April 1, 2019 as Vol. 99. Authors are invited to submit their work to this topical issue.
Authors wishing to submit their manuscript should contact editorial office via e-mail by the end of May, 2018. Manuscript should reach the editorial office no later than September 10, 2018.
Contact: submit@heterocycles.com

March 5, 2018

Heterocycles Award
HETEROCYCLES is pleased to announce Heterocycles Award.
In recognition of an outstanding oral presentation at the 47th Congress of Heterocyclic ChemistrySee more

December 13, 2017

Call for ContributionsHETEROCYCLES Special Issue Vol. 97 in honor of Professor Kiyoshi Tomioka on 70th Birthday

Submission deadline: February 15, 2018
On the occasion of Professor Kiyoshi Tomioka's 70th birthday, HETEROCYCLES editorial office is planning to publish special anniversary issue on September 1, 2018 as Vol. 97. Authors are invited to submit their work to this topical issue.
Authors wishing to submit their manuscript should contact editorial office via e-mail by the end of November, 2017. Manuscript should reach the editorial office no later than February 15, 2018.
Contact: submit@heterocycles.com

■ Formation of Thiocyanates by Ring Cleavage from 2-Imino-5,6-dihydro-4H-1,3-thiazine

Abstract

The reaction of 2-imino-5,6-dihydro-4H-1,3-thiazine with diethyl chlorophosphate, diethyl chlorothiophosphate and p-toluenesulfonyl chloride in the presence of base gave N-propylthiocyanate derivatives of diethyl phosphoramide, diethyl phosphorothioamide and p-toluenesulfonamide, respectively, in goad yield.

■ The Directed Lithiation of Isogramine and Subsequent Reactions with Electrophiles in the Preparation of 2-Substitutes Isogramine Derivatives

Dennis J. Hlasta* and Malcolm R. Bell

*Sterling Research Group, Rensselaer, New York 12144, U.S.A.

Abstract

Isogramine (1) undergoes 2-lithiation on reaction with n-butyllithium under very practical and straightforward reaction conditions. This 2-lithio species (2) reacts with aromatic carbonyl compounds to afford in good yields 2-substituted isogramines(3).

■ Ring Construction of Bicyclic-β-lactam by Use of Palladium Catalyzed Carbonylation

Abstract

Palladium catalyzed carbonylation Into vlnyl halide 10 afforded carbacepham 11 in good yield. The introduction of methoxycarbonyl group at C-4 position of carbacepham was achieved by conversion of methoxy group introduced by anodic oxidation in MeCN-MeOH to carboxyl group.

■ Bicornin, A New Hydrolyzable Tannin from Trapa bicronis, and Revised Structure of Alnusiin

Abstract

Previously proposed structure (1) for alnusiin, a hydrolyzable tannin isolated from Alnus sieboldiana, has been revised to 2, based on the 1H-13C long-range shift correlation spectroscopy. Bicornin (10), a new tannin was isolated from Trapa bicornis and its structure related to alnusiin was determined.

■ Studies on Aconitum Species. VIII. Components of "Kako-Bushi-Matsu"

Abstract

Seventeen C19-diterpenoid alkaloids were isolated from the processed aconite, “Kako-bushi-mats”. Structures of those compounds were determined on the basis of their spectral and chemical data. It was demonstrated that 15-keto-pyro type compounds 10, 11, and 15-20 were induced by heating of aconitine mesaconitine, jesaconitine, and hypaconitine present in the raw aconite roots.

Abstract

The hindered rotation about four direct bonds between the [2.2]paracyclophanyl substituents and the meso carbon centers of porphyrin in the title compound results in the appearance of many stereoisomers, some of them representing the type of stereoisomerism which had never been encountered before in porphyrin chemistry.

■ Novel Exchange Reaction of 2-Imino or 2-Thiono Derivatives of 1,3-Thiazines and 1,3-Oxazines with p-Toluenesulfonyl Isocynate

Abstract

The reaction of 2-arylimino-1,3-thiazine with p-toluenesulfonyl isocyanate led to the formation of 2-(p-toluenesulfonyl)imino-1,3-thiazine. A similar reaction carried out with 1,3-thiazine-2-thione and 1,3-oxazine-2-thione gave 2-(p-toluenesulfonyl)imino-1,3-thiazine or 1,3-oxazine, respectively.

Abstract

Trimethylsilyl enol ethers of aldehydes and acycilc or cyclic ketones react with carbon suboxide to give substituted 4-[(trimethylsilyl]oxy]-2H-pyran-2-ones in good yields, which were treated with water to afford the corresponding 4-hydroxy-2~-pyran-2-ones.

■ Convenient Preparation of Iridodial by Reduction of Nepetalactone. Corroboration for the Role of Iridodil as an Indole Alkaloid Precursor in a Catharanthus roseus Cell Suspension

John Balsevich* and Greg Bishop

*Plant Biothchnology Institute, National Research Council of Canada, Saskatoon, Saskatchewan, S7N, OW9, Canada

Abstract

Iridodial of high isomeric purity was effectiveiy prepared by reduction of nepetalactone with sodium borohydride in tert-butanol. Nepetalactone, in turn was readily obtained by steam distillation of the aerial parts of Nepeta cataria. Feeding of deuterium-labelled iridodial prepared as above and deuterium-labelled material prepared by acid-promoted cyclization of 10-oxocitronellal, to a Catharanthus roseus cell suspention culture, afforded the alkaloid, ajmalicine, which was specifically labelled with deuterium to the extent of 76% and 36%, respectively.

■ The Structure and Nmr Spectra of Some Diels-Alder Adducts of Nitrosobenzene, p-Nitrosotoluene and 1-Chloro-1-nitrosocyclohexane

Abstract

The products of the following Diels-Alder reactions have been investigated: (i) nitrosobenzene with 2-phenyl-1,3-butadiene, isoprene. piperylene, 2,3-dimethyl-1,3-butadiene, 2-methyl-3-phenyl-1,3-butadiene and 2,4-hexadiene; (ii) p-nitrosotoluene with 2,4-hexadiene: (iii) 1-chloro-1-nitrosocyclohexane with 2-methyl-3-phenyl-1,3-butadiene and 1-phenyl-1,3-pentadiene. The 4-methyl and 4-phenyl isomers are formed in relatively larger quantities in the diene reaction of isoprene and 2-phenyl-1,3-butadiene with nitrosobenzene, while the 4-methyl-5-phenyl isomer is the major product from the reaction of 2-methyl-3-phenyl-1,3-butadiene with 1-chloro-1-nitrosocyclohexane.

■ Alkylation and Arylation of Pyrazines by Organoboron Compounds

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

By palladium-catalyzed cross-coupling reactions of chloropyrazines with organoboron compounds prepared from Grignard reagents, various alkyl and aryl groups were successfully introduced into the pyrazine ring.

■ Synthesis of 2-Methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ol Derivatives by a Novel Insertion of Aryl-Nickel Complexes

Abstract

2-Methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ol derivatives (1a-j) as a new potentiator of noradrenaline were prepared by a novel intramolecular insertion of the aryl-nickel complexes of N-(2-halobenzyl) phenacylamines (2a-m).

Abstract

The 1,3-dipolar cycloadditions of acetylenic esters 1-3 with diazo compounds, sydnones and p-methoxyphenyl azide proceed in good yields and afford functionalized pyrazoles and triazoles. Cycloadditions with the acetal 1 occur with high regioselectivity, whereas the reactions with the alcohol 3 are less selective. The aldehyde 2 is more reactive than 1 or 3 and cycloadditions proceed with lower regioselectivity, normally in opposite sense with respect to 1.

*Department of Chemistry and Pharmacology, Divisional Research and Development, Fisons Pharmaceuticals, Rochester, New York 14623, U.S.A.

Abstract

The synthesis of a series of novel substituted spiro[pyrrolidine-5,2’-tricyclo[3.3.1.13,7]decane] derivatives 5-13 is described. When tested in the carrageenin-induced rat paw edema assay, several analogues elicited anti-inflammatory activity.